Due to global climate change, droughts are likely to become more frequent and more severe in many regions such as in South Africa. In Limpopo, observed high climate variability and projected future climate change will likely increase future maize production risks. This paper evaluates drought patterns in Limpopo at two representative sites. We studied how drought patterns are projected to change under future climatic conditions as an important step in identifying adaptation measures (e.g., breeding maize ideotypes resilient to future conditions). Thirty-year time horizons were analyzed, considering three emission scenarios and five global climate models. We applied the WOFOST crop model to simulate maize crop growth and yield formation over South Africa’s summer season. We considered three different crop emergence dates. Drought indices indicated that mainly in the scenario SSP5-8.5 (2051–2080), Univen and Syferkuil will experience worsened drought conditions (DC) in the future. Maize yield tends to decline and future changes in the emergence date seem to impact yield significantly. A possible alternative is to delay sowing date to November or December to reduce the potential yield losses. The grain filling period tends to decrease in the future, and a decrease in the duration of the growth cycle is very likely. Combinations of changed sowing time with more drought tolerant maize cultivars having a longer post-anthesis phase will likely reduce the potential negative impact of climate change on maize.